12/16/25 Newsletter

By the end of the tax year, the IRS is expected to have collected more than $5 trillion in gross tax revenue, processed over 266 million tax returns, and nearly half a trillion dollars in tax refunds. That’s a lot of -illions. Source: IRS Data Book

This week’s lineup:

• ⚠️ Liens and levies hit fast when you ignore IRS mail.

• 🎬 Creators get slammed when they mix money or ignore taxable “freebies.”

• 🩺 Medical bills help only after you clear the 7.5 percent hurdle.

• 🥊 Mike Tyson made $400 million and still lost to the IRS.

IRS Survival Guide

⚠️ Liens, Levies, and Staying Sane

Let's say you forgot to pay your taxes. Or you remembered, briefly, before getting distracted by a squirrel or a root canal or whatever else people do when they're actively ignoring IRS letters. Either way, you now find yourself facing two terrifyingly medieval-sounding words: lien and levy.    

Take a deep breath. Contrary to popular belief, the IRS does not teleport into your living room, snatch your espresso machine, and ride off in your new Hyundai Elantra. There's a process. Even better, it's actually one you can manage, as long as you don't bury your head in the audit sands.

File, Answer the Mail, and Keep Breathing

The IRS may be many things — relentless, humorless, suspicious of your "business use" of a jet ski — but it is also weirdly procedural. If you file your tax return and respond to notices, even if you're late, your world stays negotiable. Interest and penalties accrue, sure, but so do options.  

Ignore their letters, though, and things start to escalate faster than your blood pressure while waiting in line at the DMV.

Lien vs. Levy: The Bare Minimum You Need to Know

First comes a lien, essentially the IRS writing their name on your stuff. A lien says, "You still own this, but we have dibs." It's public, it's annoying, and yes, it can impact your ability to get a loan. But it's not the same as a levy, which is when the IRS goes from writing their name on your stuff to physically taking it.  

The good news? There are ways to reverse, remove, or finesse a lien. You can request a withdrawal (Form 12277), pay in full (crazy, we know), or negotiate a payment plan that makes the lien less bite-y. Just don't sit there hoping it'll go away. It won't. The IRS is not a bad dream you can wake up from. They will remember you exist.

Want the part that everybody gets wrong about liens and levies? Keep reading →

Business & Gigs

🎬 Creator Tax Traps to Avoid

It takes years to build a brand.

It takes one envelope from the IRS to make it feel like it could all vanish overnight.

Ask any creator who's been there. One minute, you're celebrating a six-figure year built on brand deals and ad revenue. The next, you're staring at a tax bill with so many zeros it looks like a typo — plus a mountain of penalties for not paying taxes you didn't even know you owed.

Suddenly, you're not an influencer anymore. You're an "in-default-cer." And nothing kills a brand faster than the quiet panic of a massive, public tax lien.

This isn't a scare tactic. It's a story that happens every single year. But it doesn't have to be yours. That cautionary tale is just what happens when you commit a few cardinal sins of creator finance.

See the three tax mistakes that wreck creator brands. Read now→

Money Moves

🩺 Medical Bills and the IRS: What Actually Counts

Nobody wants to qualify for the medical expense deduction.

It usually means you've had a year filled with unpleasant appointments, bewildering bills, and more time spent in a waiting room than you'd care to remember. It’s the tax break you earn through sheer misfortune.

But if you've weathered that storm, the IRS offers a small, complicated, but potentially valuable, consolation prize. It's their way of saying, "That sounds rough. Here, let's haggle over the details."

The First, and Highest, Hurdle: The 7.5 Percent Rule            

Before you start dreaming of tax-deductible gold fillings, you must face the gatekeeper of this deduction: the 7.5 Percent of Adjusted Gross Income (AGI) rule.

It’s a concept so brilliantly simple and yet so maddeningly difficult to achieve, a committee of marathon runners must have designed it.

First, you must be willing to do the paperwork. This deduction is only available to those who itemize deductions on a Schedule A, foregoing the convenience of the standard deduction.

Second, you have to clear the bar. You can only deduct the amount of your unreimbursed medical expenses that is more than 7.5 percent of your AGI.

Think of it this way: If your AGI is $60,000, your personal hurdle is $4,500 ($60,000 x 0.075). You have to spend that much out-of-pocket before the IRS even starts counting.

If your total medical bills for the year were $5,000, you would get to deduct a mere $500 ($5,000 minus $4,500). It’s a tough club to get into.

Want to know which medical expenses actually qualify? Keep reading →

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Wild Tax Tales

🥊 Mike Tyson vs. The IRS

Mike Tyson earned roughly $400 million over his career, a number so huge it barely feels real. For most people, that’s a lifetime of security. For Tyson, it became the launchpad for one of the fastest financial wipeouts in modern celebrity history.

He didn’t just spend money. He detonated it. His shopping list included more than 100 luxury cars, a two-million-dollar solid-gold bathtub, and three Bengal tigers with price tags big enough to require their own accountants. Mansions, jewelry, and high-maintenance pets piled up faster than the bills that followed them.

While the spectacle played out in public, a quieter opponent waited in the background. The IRS doesn’t care about knockout power or pop-culture fame. It cares about unpaid taxes. By 2003, Tyson filed for bankruptcy with $23 million in debt. More than half of it belonged to Uncle Sam. Another $4 million was owed to British tax authorities. Even the tigers weren’t impressed.

The comeback wasn’t flashy. It was slow, disciplined, and painfully human. Tyson took movie roles, toured with a one-man show, launched a cannabis company, and even returned to the ring. Piece by piece, he chipped away at the debt. As part of his bankruptcy settlement, he repaid about $9 million to the IRS, finally clearing the tax burden by 2007.

His story is wild, sure, but the lesson is simple. No matter how much you earn, how famous you are, or how many exotic animals you own, you can’t outrun the taxman.

The quick (and slightly prickly) stories we didn’t have time to get to:

• 🐶 A lawyer wants pets recognized as tax dependents, but the IRS is likely to shut it down.

• 🚨 IRS investigations uncovered $10.6B in financial crimes as enforcement ramped up.

• 🎓 A new 2027 tax credit offers up to $1,700 for donations to K–12 scholarship programs.

If you made it this far, you’re our kind of nerd. Hit reply and tell us which story you want us to dive deeper into next week.

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